I thought is was this December? You only have 3 months. That is not a lot of time.

Another US based suggestion would be Georgia. You could even drive there from Chicago. Georgia has lots of pretty little towns to explore.

As far as Asia. As I suggested why not consider a combo tour / vacation spot? You could back bags for a few overnights and for a ride from a "home base". Don't be afraid to use a train or a bus to get you out of the city if that is were you decide to stay. Something like that would require a lot less planning. Just pick a location, throw some stuff in a bag and go. Return to your home base and repeat the next day or two. You would get your adventure without too much risk. Heck just going to Asia is an adventure on its own.

With your 40 mile limit, that is going to require some real planning if you want to do a multi day tour. No matter where you stay tent or hotel, you will need a place each night. Not too awfully difficult to plan but 3 months is not a whole lot of time to figure out where to stay, what route to take etc etc. Personally I would want at least a year to plan such a tour. Something like the Great Allegheny Passage that I have done so many times, yeah give me a couple of hours to pack and I am off. But Asia? That would take me some time to plan.